It sounds like you are missing lots of warm up and working your way up to accepting a full fledged member into your anus. You might search some other posts in the forum like this one that is full of great advice.

Lots of lube is a must. Being able to relax is helpful. Anal sex is fantastic when done right and should not hurt. It is not for everyone though. Go SLOW!

Lots and lots of lube and lots and lots of patience is the key when beginning. Going too fast and getting hurt and being in pain will turn people off and they won't want to try again for a long time... maybe forever. Just start off with a very smooth and well lubed tiny toy or a pinky finger and build up from there.

I feel like we are posting this information several times a month. That's OK. We're here to help.

From my experience, as a receiver: (I'm a female, my partner is male and we have anal play and anal sex. He doesn't receive anal sex, due to personal preference and the dynamic of our D/s relationship. But, he trained me to receive (and LOVE) anal sex and anal play when we both began to express an interest in it.)

Being fully aroused first really helps. I find having an orgasm or more before attempting anal sex is really very important as it relaxes me and also makes me even more aroused for more fun.

We started out SLOWLY. Just a finger or two, once I was really aroused, just kind of massaging, before any penetration was done. Fingers should be clean and lubed with a nice lube like Sliquid H2O Ride or Sliquid Booty Formula. Some people like silicone lubes for anal play, it's OK as long as you won't be using any silicone toys during this session.

He bought be a "beginner" anal toy. (The Crystal Cote Butt Plug) but at first I didn't like it. (I found out later, I prefer tear drop or roundish shaped plugs and beads better.) We went back to hands.

He also would sometimes do some rimming (oral stimulation of the outer anal area) The receiver should have just had a VERY thorough bath or shower before any rimming is attempted.

Over a period of time, at least a month, he played more and more with me, we found out that an orgasm before really helped (although now, years later, I do enjoy anal play with toys or fingers before the first time I come in each session.) We would often go back between anal play and vaginal play (NEVER using the same finger for the vagina or clitoris after it was used on the anus) PIV sex, oral play and anything else to get both of us as aroused as possible. We also had a lot of sex WITHOUT anal play. He didn't want me to feel pressured and our sex life in general didn't change.

After a period of time, as I could accept three or four fingers very comfortably and happily, we decided to attempt anal intercourse. The first time was a little strange, but done properly it SHOULD NOT HURT! If it hurts, you are doing something wrong. DO NOT use any numbing ointments or sprays. Your body should accept the anal play without being in pain and nothing should be done to stop the pain of improper technique from happening, because any pain is a signal to STOP, something is wrong!

I did have a little blood the first time we had anal sex, but I have given birth to a bunch of kids and have hemorrhoids (sorry if that's TMI, but it's part of life.) It scared me a little, so we took some time out and went back to more finger play and began to use anal toys gently. At first, my favorite was The Plug of Lust Small It's a GREAT starter toy.

I've moved on to other toys, both plugs and beads since then. I have to say that NONE of my training consisted of wearing a butt plug for anything other than sex. I don't walk around wearing one. Some people do this and like it, but it doesn't ring everyone's bell. Long term wear of butt plugs does NOT have to be part of anal play training.

My Man had the idea that since I love PIV sex (penis in vagina intercourse) that using a dildo or phallic vibrator in my vagina before and during anal sex would make me more comfortable. I have to say this was a stroke of genius. Most women are comfortable enough with vaginal penetration, and it's familiar enough to relax her even further. We tried this (sometimes with the vibrator on and sometimes with it just in place) and we really started to have a good time!

We often have anal sex and anal play and it really depends on what either of us are in the mood for.

It probably took a month or more of "training" to be able to accept a full penis. No "just sticking it in and gritting your teeth" THAT isn't healthy, nor will you enjoy it. No man who loves his woman, or woman who loves her woman, or woman who loves her man would just expect to "stick it in" and have his or her partner be comfortable and happy.

We found that after I really found I Loved anal sex, we could use toys more easily. Some people start with toys or use them as part of their training. What YOU like is up to you and you won't know until you try.

The idea is for BOTH of you to have a good time.

I have to say, the feeling from anal sex is like an altered state. Sometimes I feel more alive and intense than any other time in my life. It's different than PIV, oral sex, finger play. It's a wonderful way to feel close to your partner. I feel so bonded to My Man when we have any kind of sex, but there's something really special about a good bout of anal sex, after a few orgasms. And OMG, the orgasms during anal sex are amazing! Just fantastic.

As you can see, I can't say enough about it.

To summarize:

Take your time. Don't expect to get a penis in there the first few days or week you are playing anally.

Cleanliness is important. Bathing before anal play is a MUST. I do not personally use an anal douche, but some people do, depending on how their digestive systems work. Some people have residue after a bowel movement every time and they probably need to douche. Other people have completely empty rectums after using the toilet, so they usually don't need to.

A well lubed finger may well be the best way to start. STOP if it hurts.

An orgasm before anal sex may help the receiver, if she is a woman, to relax and be more comfortable.

Vaginal penetration with a toy helps some women feel more accepting of anal penetration.

Lube, lube lube lube lube. Did I mention use LUBE?

STOP if it hurts.

Don't do it if you are not in the mood, your belly hurts, or you just don't feel like it.

I feel like we are posting this information several times a month. That's OK. We're here to help.

From my experience, as a receiver: (I'm a female, my partner is male and we have anal play and anal sex. He
...

I feel like we are posting this information several times a month. That's OK. We're here to help.

From my experience, as a receiver: (I'm a female, my partner is male and we have anal play and anal sex. He doesn't receive anal sex, due to personal preference and the dynamic of our D/s relationship. But, he trained me to receive (and LOVE) anal sex and anal play when we both began to express an interest in it.)

Being fully aroused first really helps. I find having an orgasm or more before attempting anal sex is really very important as it relaxes me and also makes me even more aroused for more fun.

We started out SLOWLY. Just a finger or two, once I was really aroused, just kind of massaging, before any penetration was done. Fingers should be clean and lubed with a nice lube like Sliquid H2O Ride or Sliquid Booty Formula. Some people like silicone lubes for anal play, it's OK as long as you won't be using any silicone toys during this session.

He bought be a "beginner" anal toy. (The Crystal Cote Butt Plug) but at first I didn't like it. (I found out later, I prefer tear drop or roundish shaped plugs and beads better.) We went back to hands.

He also would sometimes do some rimming (oral stimulation of the outer anal area) The receiver should have just had a VERY thorough bath or shower before any rimming is attempted.

Over a period of time, at least a month, he played more and more with me, we found out that an orgasm before really helped (although now, years later, I do enjoy anal play with toys or fingers before the first time I come in each session.) We would often go back between anal play and vaginal play (NEVER using the same finger for the vagina or clitoris after it was used on the anus) PIV sex, oral play and anything else to get both of us as aroused as possible. We also had a lot of sex WITHOUT anal play. He didn't want me to feel pressured and our sex life in general didn't change.

After a period of time, as I could accept three or four fingers very comfortably and happily, we decided to attempt anal intercourse. The first time was a little strange, but done properly it SHOULD NOT HURT! If it hurts, you are doing something wrong. DO NOT use any numbing ointments or sprays. Your body should accept the anal play without being in pain and nothing should be done to stop the pain of improper technique from happening, because any pain is a signal to STOP, something is wrong!

I did have a little blood the first time we had anal sex, but I have given birth to a bunch of kids and have hemorrhoids (sorry if that's TMI, but it's part of life.) It scared me a little, so we took some time out and went back to more finger play and began to use anal toys gently. At first, my favorite was The Plug of Lust Small It's a GREAT starter toy.

I've moved on to other toys, both plugs and beads since then. I have to say that NONE of my training consisted of wearing a butt plug for anything other than sex. I don't walk around wearing one. Some people do this and like it, but it doesn't ring everyone's bell. Long term wear of butt plugs does NOT have to be part of anal play training.

My Man had the idea that since I love PIV sex (penis in vagina intercourse) that using a dildo or phallic vibrator in my vagina before and during anal sex would make me more comfortable. I have to say this was a stroke of genius. Most women are comfortable enough with vaginal penetration, and it's familiar enough to relax her even further. We tried this (sometimes with the vibrator on and sometimes with it just in place) and we really started to have a good time!

We often have anal sex and anal play and it really depends on what either of us are in the mood for.

It probably took a month or more of "training" to be able to accept a full penis. No "just sticking it in and gritting your teeth" THAT isn't healthy, nor will you enjoy it. No man who loves his woman, or woman who loves her woman, or woman who loves her man would just expect to "stick it in" and have his or her partner be comfortable and happy.

We found that after I really found I Loved anal sex, we could use toys more easily. Some people start with toys or use them as part of their training. What YOU like is up to you and you won't know until you try.

The idea is for BOTH of you to have a good time.

I have to say, the feeling from anal sex is like an altered state. Sometimes I feel more alive and intense than any other time in my life. It's different than PIV, oral sex, finger play. It's a wonderful way to feel close to your partner. I feel so bonded to My Man when we have any kind of sex, but there's something really special about a good bout of anal sex, after a few orgasms. And OMG, the orgasms during anal sex are amazing! Just fantastic.

As you can see, I can't say enough about it.

To summarize:

Take your time. Don't expect to get a penis in there the first few days or week you are playing anally.

Cleanliness is important. Bathing before anal play is a MUST. I do not personally use an anal douche, but some people do, depending on how their digestive systems work. Some people have residue after a bowel movement every time and they probably need to douche. Other people have completely empty rectums after using the toilet, so they usually don't need to.

A well lubed finger may well be the best way to start. STOP if it hurts.

An orgasm before anal sex may help the receiver, if she is a woman, to relax and be more comfortable.

Vaginal penetration with a toy helps some women feel more accepting of anal penetration.

Lube, lube lube lube lube. Did I mention use LUBE?

STOP if it hurts.

Don't do it if you are not in the mood, your belly hurts, or you just don't feel like it.

Take your time and ENJOY!

Sorry for the wall O text.

Awesome response PGell! For me an orgasm, lube and patience were and still are the key. Perhaps also a glass of wine? I hesitate to mantion wine, but not intoxicated.
Good luck! The pleasure is so worth it..

Awesome response PGell! For me an orgasm, lube and patience were and still are the key. Perhaps also a glass of wine? I hesitate to mantion wine, but not intoxicated.

Good luck! The pleasure is so worth it..

Liz, a lot of people do relax with a glass of wine or a small drink. I'm not talking Balls To the Wall drunk, just relaxed. That seems to work well for some people.

I didn't mention it, as I don't drink and it didn't occur to me. But, as long as you are still sober, in control of your faculties and aware of what is going on, it's fine.

Of course, being too intoxicated may cause one to not notice when something should be hurting and not stop when they should change something. But, I think most adults know how much liquor they can handle and still be aware and alert. (For me, any amount is usually too much. Which is why I don't use it. ) But, most adults are fine with a little liquor to relax.